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Preparation of new N 6 , 9‐disubstituted 2‐phenyl‐adenines and corresponding 8‐azaadenines.: A feasibility study for application to solid‐phase Synthesis. I
Author(s) -
Biagi Giuliana,
Giorgi Irene,
Livi Oreste,
Pacchini Federica,
Scartoni Valerio,
Salerni Oreste Leroy
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410415
Subject(s) - chemistry , acetic anhydride , pyrimidine , medicinal chemistry , amine gas treating , yield (engineering) , acetic acid , nucleophile , triethyl orthoformate , ring (chemistry) , diethylamine , hydrochloric acid , chlorine , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
A suitably substituted pyrimidine 1 was converted to a number of title compounds. Nucleophilic substitu tion involving the chlorine atoms in 1 by treatment with phenylmethanethiol yielded 2 or 3 , depending on the reaction temperature. Treatment of 3 with an amine afforded 6‐phenylmethanesulfanyl‐N 4 ‐substituted‐2‐phenyl‐pyrimidine‐4,5‐diamines 4–7 . These pyrimidines were converted into 2‐phenylpurines 8–11 and 2‐phenyl‐8‐azapurines 12–14 , by treatment with triethyl orthoformate in the presence of hydrochloric acid (or acetic anhydride), or with potassium nitrite and acetic acid respectively. The thioether function on C(6) was then converted into a sulfonyl group by oxidation with m ‐chloroperoxybenzoic acid affording purines 15–18 and their 8‐azaanalogs 19–21 ; these compounds, as crude products, were treated with an amine to yield the corresponding adenines 22–25 or 8‐azaadenines 26–31. All reactions were performed under conditions com patible with the possible use of a thiomethyl resin in place of phenylmethanethiol to bind the pyrimidine ring of 1 to a solid phase.